The Chemistry of Heterocyclic Compounds, since its inception, has been recognized as a cornerstone of heterocyclic chemistry. Each volume attempts to discuss all aspects - properties, synthesis, reactions, physiological and industrial significance - of a specific ring system. To keep the series up-to-date, supplementary volumes covering the recent literature on each individual ring system have been published. Many ring systems (such as pyridines and oxazoles) are treated in distinct books, each consisting of separate volumes or parts dealing with different individual topics. With all authors are recognized authorities, the Chemistry of Heterocyclic Chemistry is considered worldwide as the indispensable resource for organic, bioorganic, and medicinal chemists.
Autorentext
W. C. Sumpter is the editor of Heterocyclic Compounds with Indole and Carbazole Systems, Volume 8, published by Wiley.
F. M. Miller is the editor of Heterocyclic Compounds with Indole and Carbazole Systems, Volume 8, published by Wiley.
Zusammenfassung
The Chemistry of Heterocyclic Compounds, since its inception, has been recognized as a cornerstone of heterocyclic chemistry. Each volume attempts to discuss all aspects properties, synthesis, reactions, physiological and industrial significance of a specific ring system. To keep the series up-to-date, supplementary volumes covering the recent literature on each individual ring system have been published. Many ring systems (such as pyridines and oxazoles) are treated in distinct books, each consisting of separate volumes or parts dealing with different individual topics. With all authors are recognized authorities, the Chemistry of Heterocyclic Chemistry is considered worldwide as the indispensable resource for organic, bioorganic, and medicinal chemists.
Inhalt
I. Indole 1
Introduction 1
Synthesis of Indole 3
Oxidation of Indole 23
Tautomerism of Indole 25
Sulfonation of Indole 28
Halogen Derivatives of Indole 29
Alkyl Derivatives of Indole 31
Indoline 36
Metal Salts of Indole 40
Indole Aldehydes 40
Acyl Derivatives of Indole 44
Condensation of Indoles with Aldehydes 48
Indolylmagnesium Halides 50
Indole Polymers 61
Preparation and Reactions of Gramine 62
Carboxylic Acids of the Indole Series 65
II. Carbazole 70
Introduction 70
Preparation of Carbazole 72
Graebe-Ullman Synthesis 72
Method of Borsche 73
Other Methods of Synthesis of Carbazoles 78
Nitro Derivatives of Carbazole 81
Aminocarbazoles 85
Halogen Derivatives of Carbazole 87
Carbazolesulfonic Acids 91
Reduction of Carbazole 93
Oxidation of Carbazole 96
Carbazyl Aldehydes and Ketones 97
Carbazole Carboxylic Acids 101
N-Acyl Carbazoles 104
N-Alkyl Carbazoles 105
III. Isatin 110
Preparation of Isatin 111
Properties of Isatin 114
Tautomerism 115
Reactions of Isatin 116
Oxidation and Reduction 116
Halogenation and Nitration 118
Acylation and Alkylation 120
Reactions of the Carbonyl Groups 121
Grignard Reagents 121
Amine Derivatives 122
Miscellaneous Reagents 126
Active Methylene Groups 127
Biological Activity of Isatin 132
Analytical Uses of Isatin 133
IV. Oxindole 134
Preparation of Oxindoles 134
Properties of Oxindoles 138
Tautomerism 138
Salts 138
Reactions of Oxindole 139
Reduction 139
Halogenation and Nitration 140
Condensation Reactions 142
Alkylation and Acylation 146
Derivatives 148
Hydroxyoxindoles 148
Dioxindole 148
1 -Hydroxyoxindole 151
Aminooxindoles 151
3, 3-Diaryloxindoles 152
V. Isatogens 154
VI. Indoxyl 163
Introduction 163
Synthesis of Indoxyl 163
Physical Properties 165
Reactions 165
Acyl Derivatives of Intloxyl 167
Indoxyl Sulfuric Acid 168
Indican 168
Indoxylic Acid and Indoxyl-2-aldehyde 169
VII. Indigo 171
Introduction 171
Occurrence of Indigo 174
Synthesis of Indigo 175
Physical Properties of Indigo 178
Chemical Properties of Indigo 179
Formation of Salts 179
Oxidation of Indigo 180
Imides and Oximes of Indigo 181
Reduction of Indigo 182
Halogenated Indigos 184
Alkyl and Acyl Derivatives of Indigo 189
Preparation of Indigoids 191
Isoindigo and Indirubin 192
VIII. Natural Products Containing the Indole Nucleus 196
Simple Bases 196
Gramine 196
Donaxarine 197
Tryptophan 197
Serotonin 199
Abrine 200
Hypaphorine 200
Bufotenines 201
Dipterine 202
Calabar Alkaloids 203
Physostigmine 203
Geneserine 207
Harmala Alkaloids 208
Harmaline, Harmine, and Harmalol 208
Harman 213
Eleaginine 213
Leptocladine 213
Calycanthine 214
Calycanthidine 216
Folicanthine 217&...